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TG(12:0/12:0/18:1(9Z)) (YMDB01260)

Identification
YMDB IDYMDB01260
NameTG(12:0/12:0/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTG(12:0/12:0/18:1(9Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). TG(12:0/12:0/18:1(9Z)) may be a unique S. cerevisiae (yeast) metabolite. Within yeast, TG(12:0/12:0/18:1(9Z)) participates in a number of enzymatic reactions. In particular, TG(12:0/12:0/18:1(9Z)) can be biosynthesized from DG(12:0/18:1(9Z)/0:0) through its interaction with the enzyme diacylglycerol O-acyltransferase 1. In addition, TG(12:0/12:0/18:1(9Z)) can be converted into DG(12:0/18:1(9Z)/0:0) through its interaction with the enzyme triacylglycerol lipase complex. In yeast, TG(12:0/12:0/18:1(9Z)) is involved in the metabolic pathway called the triacylglycerol metabolism tg(12:0/12:0/18:1(9z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-dodecanoyl-2-dodecanoyl-3-oleoyl-glycerol
  • TAG(12:0/12:0/18:1)
  • TAG(12:0/12:0/18:1n9)
  • TAG(12:0/12:0/18:1w9)
  • TAG(42:1)
  • TG(12:0/12:0/18:1)
  • TG(12:0/12:0/18:1n9)
  • TG(12:0/12:0/18:1w9)
  • TG(42:1)
  • Tracylglycerol(12:0/12:0/18:1)
  • Tracylglycerol(12:0/12:0/18:1n9)
  • Tracylglycerol(12:0/12:0/18:1w9)
  • Tracylglycerol(42:1)
  • Triacylglycerol
  • Triglyceride
CAS numberNot Available
WeightAverage: 721.161
Monoisotopic: 720.626790425
InChI KeyVHSCSWKCDUHRCW-VAVOUJMRSA-N
InChIInChI=1S/C45H84O6/c1-4-7-10-13-16-19-20-21-22-23-24-27-29-32-35-38-44(47)50-41-42(51-45(48)39-36-33-30-26-18-15-12-9-6-3)40-49-43(46)37-34-31-28-25-17-14-11-8-5-2/h21-22,42H,4-20,23-41H2,1-3H3/b22-21-/t42-/m0/s1
IUPAC Name(2S)-2,3-bis(dodecanoyloxy)propyl (9Z)-octadec-9-enoate
Traditional IUPAC Name(2S)-2,3-bis(dodecanoyloxy)propyl (9Z)-octadec-9-enoate
Chemical FormulaC45H84O6
SMILES[H][C@](COC(=O)CCCCCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCCC
Chemical Taxonomy
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.1e-05 g/LALOGPS
logP10.32ALOGPS
logP15.89ChemAxon
logS-7.8ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity214.8 m³·mol⁻¹ChemAxon
Polarizability94.87 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Triacylglycerol metabolism TG(12:0/12:0/18:1(9Z))PW007621 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
long-chain fatty acyl-CoA + DG(12:0/18:1(9Z)/0:0) → Coenzyme A + TG(12:0/12:0/18:1(9Z))
TG(12:0/12:0/18:1(9Z)) + water → hydron + Fatty Acid + DG(12:0/18:1(9Z)/0:0)
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
4750 ± 500 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004k-0000990000-aa876e088e8323798222JSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider ID24608139
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Diacylglycerol O-acyltransferase 1
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for storage lipid synthesis. May be involved in lipid particle synthesis from the endoplasmic reticulum and ergosterol biosynthesis
Gene Name:
DGA1
Uniprot ID:
Q08650
Molecular weight:
47710.89844
Reactions
Acyl-CoA + 1,2-diacylglycerol → CoA + triacylglycerol.
Protein Details
2. Sterol esterase TGL1
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo
Gene Name:
TGL1
Uniprot ID:
P34163
Molecular weight:
62978.39844
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
Protein Details
3. Lipase 2
General function:
Involved in hydrolase activity, acting on ester bonds
Specific function:
Lipolytic activity towards triacylglycerols and diacylglycerols with short-chain fatty acids
Gene Name:
TGL2
Uniprot ID:
P54857
Molecular weight:
37499.89844
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
4. Lipase 3
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process
Gene Name:
TGL3
Uniprot ID:
P40308
Molecular weight:
73611.79688
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
5. Lipase 5
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL5
Uniprot ID:
Q12043
Molecular weight:
84715.10156
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
6. Lipase 4
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL4
Uniprot ID:
P36165
Molecular weight:
102716.0
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.